Phenylhydrazine → N'-phenyl-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carbohydrazide

HRID 704433Notes

Reaction equation

HRID 704433 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][C:21]([N:23]1[CH:27]([C:28]([OH:30])=O)[CH2:26][S:25][CH:24]1[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[C:37]1([NH:43][NH2:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.ON1C2C=CC=CC=2N=N1>O1CCCC1.C(OCC)(=O)C>[C:37]1([NH:43][NH:44][C:28]([CH:27]2[CH2:26][S:25][CH:24]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[N:23]2[C:21]([O:20][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22])=[O:30])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 7516PhenylhydrazineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14772789N-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 20074037N'-phenyl-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carbohydrazideYield 95.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 450 mg of dicyclohexylcarbodiimide in 5 ml of tetrahydrofuran was added dropwise to a mixture of 680 mg of N-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid, 240 mg of phenylhydrazine, 450 mg of 1-hydroxybenzotriazole and 20 ml of tetrahydrofuran with ice cooling, and the resultant mixture was stirred with ice cooling for 1 hour and then at room temperature for 12 hours. The reaction mixture was diluted with 30 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate Concentration under reduced pressure gave 840 mg of N'-phenyl-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carbohydrazide. Trifluoroacetic acid (5 ml) was added to the thus-obtained compound, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and the solution was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate Concentration under reduced pressure gave crystals, which were recrystallized from ethyl acetate. Thus was obtained 180 mg of N'-phenyl- 2-(3-pyridyl)thiazolidine-4-carbohydrazide. Melting point 155° C.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate Concentration under reduced pressure

Sources & evidence

ORD record
ord-18aeec0c22244596b8360254318179aa
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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